Theoretical Study of the Mechanisms of Acid-Catalyzed Amide Hydrolysis in Aqueous Solution

2003 ◽  
Vol 107 (44) ◽  
pp. 12303-12306 ◽  
Author(s):  
Dirk Zahn
Keyword(s):  
Aqueous Solution ◽  
Theoretical Study ◽  
Amide Hydrolysis ◽  
Acid Catalyzed

Intramolecular nucleophilic participation by the thiol group during amide hydrolysis. Part 2. The imidazole catalysis dilemma

1992 ◽  
Vol 70 (1) ◽  
pp. 62-67 ◽  
Author(s):  
Robert S. McDonald ◽  
Patricia Patterson ◽  
June Rodwell ◽  
Ann Whalley
Keyword(s):  
Aqueous Solution ◽  
Thiol Group ◽  
Tetrahedral Intermediate ◽  
General Base ◽  
General Acid ◽  
Amide Hydrolysis ◽  
Acid Catalyzed ◽  
Rate Limiting ◽  
Imidazole Catalysis

Catalysis by imidazole and N-methylimidazole buffers of the intramolecular thiolysis of N-n-propyl 2-mercaptomethylbenzamide (forming 2-thiophthalide) has been studied in aqueous solution at 40.0 °C, μ = 1.0. Unlike other buffers previously studied, imidazole and N-methylimidazole are able to catalyze, by a general base route, formation of neutral tetrahedral intermediate; this pathway is rate limiting at pH ≤ 7.5. At higher pH, the previously reported general acid-catalyzed breakdown of this intermediate is rate limiting. The relevance of these observations to the currently accepted pathway for the acylation of papain by amide substrates is discussed. Keywords: amide hydrolysis, intramolecular, thiol participation, imidazole, papain model.

Meso tetrakis ortho-, meta-, and para-N-alkylpyridiniopor-phyrins: kinetics of copper(II) and zinc(II) incorporation and zinc porphyrin demetalation

2003 ◽  
Vol 07 (03) ◽  
pp. 139-146 ◽  
Author(s):  
Peter Hambright ◽  
Ines Batinić-Haberle ◽  
Ivan Spasojević
Keyword(s):  
Aqueous Solution ◽  
Ionic Strength ◽  
Effective Charge ◽  
Methyl Ethyl ◽  
Ionic Strength Dependence ◽  
Zinc Porphyrin ◽  
Cationic Porphyrin ◽  
Strength Dependence ◽  
Acid Catalyzed ◽  
Kinetics Of

The relative reactivities of the tetrakis( N -alkylpyridinium- X - yl )-porphyrins where X = 4 (alkyl = methyl, ethyl, n -propyl) , X = 3 (methyl) , and X = 2 (methyl, ethyl, n -propyl, n -butyl, n -hexyl, n -octyl) were studied in aqueous solution. From the ionic strength dependence of the metalation rate constants, the effective charge of a particular cationic porphyrin was usually larger when copper(II) rather than zinc(II) was the reactant. The kinetics of ZnOH + incorporation and the acid catalyzed removal of zinc from the porphyrins in 1.0 M HCl were also studied. In general, the more basic 4- (para-) and 3- (meta-) isomers were the most reactive, followed by the less basic 2- (ortho-) methyl to n -butyl derivatives, with the lipophilic ortho n -hexyl and n -octyl porphyrins the least reactive.

Synthetic and Mechanistic Aspects of Acid-Catalyzed Disproportionation of Dialkyl Diarylmethyl Ethers: A Combined Experimental and Theoretical Study

2009 ◽  
Vol 2009 (25) ◽  
pp. 4346-4351 ◽  
Author(s):  
Margherita Barbero ◽  
Stefano Bazzi ◽  
Silvano Cadamuro ◽  
Stefano Dughera ◽  
Giovanni Ghigo
Keyword(s):  
Theoretical Study ◽  
Acid Catalyzed

Why is glycine a zwitterion in aqueous solution? A theoretical study of solvent stabilising factors

1996 ◽  
Vol 260 (1-2) ◽  
pp. 21-26 ◽  
Author(s):  
F.R. Tortonda ◽  
J.L. Pascual-Ahuir ◽  
E. Silla ◽  
I. Tuñón
Keyword(s):  
Aqueous Solution ◽  
Theoretical Study

THE CHEMISTRY OF ETHYLENE OXIDE: V. THE REACTION OF ETHYLENE OXIDE WITH HALIDE IONS IN NEUTRAL AND ACID SOLUTION

1952 ◽  
Vol 30 (3) ◽  
pp. 169-176 ◽  
Author(s):  
A. M. Eastham ◽  
G. A. Latremouille
Keyword(s):  
Aqueous Solution ◽  
Ethylene Oxide ◽  
Acid Solution ◽  
Activation Energies ◽  
Hydrogen Halide ◽  
Halide Ions ◽  
Neutral Aqueous Solution ◽  
Rate Of Hydrolysis ◽  
Acid Catalyzed ◽  
Hydrolysis Of

The rates of reaction of halide ions with ethylene oxide in neutral aqueous solution and the rate of hydrolysis of ethylene oxide in acid solution have been measured and the activation energies determined. From these data and from the ratio of glycol to chlorohydrin formed when ethylene oxide reacts with excess aqueous hydrogen halide, the rates of the acid-catalyzed addition of halide ions to ethylene oxide at 25 °C. have been estimated.

Conversion of Glycerol to Lactic Acid Catalyzed by Different-Sized Cu2O Nanoparticles in NaOH Aqueous Solution

2017 ◽  
Vol 17 (1) ◽  
pp. 780-787 ◽  
Author(s):  
Lingqin Shen ◽  
Haixu Yin ◽  
Hengbo Yin ◽  
Si Liu ◽  
Aili Wang
Keyword(s):  
Aqueous Solution ◽  
Lactic Acid ◽  
Cu2o Nanoparticles ◽  
Acid Catalyzed

scholarly journals Mechanism and theory of d-glucopyranose homogeneous acid catalysis in the aqueous solution phase

2019 ◽  
Vol 21 (32) ◽  
pp. 17993-18011 ◽  
Author(s):  
Manik Kumer Ghosh ◽  
Mícheál Séamus Howard ◽  
Karla Dussan ◽  
Stephen Dooley
Keyword(s):  
Aqueous Solution ◽  
Acid Hydrolysis ◽  
Acid Catalysis ◽  
Theoretical Study ◽  
Solution Phase ◽  
Homogeneous Acid ◽  
Hydrolysis Of

Theoretical study of the mechanism of acid hydrolysis of β-d-glucopyranose in the aqueous solution.

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